One of the classic brand-extension blunders of all time has to be when toothpaste-maker Colgate decided to come out with a line of frozen dinners. The story is told in many places, and it's usually described as having occurred in 1982. For instance, here's the HuffPost's take on it:
We suppose the idea behind Colgate Kitchen Entrees was the fact that you’d eat the Colgate frozen dinner and then brush your teeth with Colgate toothpaste, but this one just simply didn’t work. The frozen food market was already pretty saturated when these dinners were released in 1982, and when people think of Colgate they tend to think of clean teeth, not frozen Swedish meatballs.
Lots of other sites refer to this as having happened in 1982, such as here, here, and here. But when I took a closer look at the story I couldn't find any primary sources from 1982 about it. But there are several 1960s-era sources (Washington Food Report, Weekly Digest) that refer to Colgate having test-marketed a line of frozen dinners in Madison, Wisconsin in 1964. A 1966 article in Television Age magazine offered some insight into what inspired the company to do this:
To enlarge its business, now dependent almost entirely on soaps and toiletries against the P&G and Lever competition, Colgate has long wanted to get into the $4.2-billion convenience food field. Its efforts here have been fruitless. A line of dried chicken and crabmeat entrees under a Colgate Kitchen label was introduced and quickly withdrawn. An apple-chip called Snapples has been tested off-and-on over a two-year period, and one or two other food items are in various stages. The company has specialty foods operations in France and Italy, but evidently is finding it hard to duplicate their success here.
So, unless someone can find some primary sources that indicate otherwise, I'm going to assume that the Colgate Kitchen debacle actually happened in 1964, not 1982. And it was only a test-marketing trial run, not a full product roll-out. It would definitely be bizarre if, after the 1964 failure, Colgate tried the same thing again in 1982.
Why did we [initially] focus on the male market? As consumers, we had spent years wondering why dairy companies were purposefully and squarely catering to women, while overlooking the other half of the population. Research showed that dairy products were an ideal, healthy source of protein that could be a filling and high-octane component of the male diet, but there weren’t any offerings that were encouraging men to fuel up on healthy dairy products rather than highly processed snack foods and synthetic protein powders...
The massive positive response from active women and men alike pushed the brand to fully evolve to an active lifestyles brand in late 2013. It was clear that Powerful had struck a chord with active people across the world, even being named “Best Yogurt” at the 2013 World Dairy Congress in Switzerland.
I'm guessing online mockery also played a role in their change of focus.
One of the most notorious marketing failures in the beer industry: Miller's decision to create a beer that not only tasted like water, but looked like it as well. It was an outgrowth of the "clear craze" of the 1980s and 90s (making transparent products because, as wikipedia notes, "clarity was equated with purity and freedom from artificial dyes").
Johnston's Hot Scoop Microwave Sundae is one of those products where you have to wonder what was going through the minds of the executives who dreamed it up. Introduced in the mid-1980s, the concept was that it was an entire, frozen ice cream sundae that you could heat in the microwave, and (in theory) only the topping would melt.
In practice, the ice cream also inevitably melted, leaving consumers with a soggy mix of ice cream and topping. And yet the company went to all the effort to make this thing because they figured it would be too difficult for people to just heat the topping on its own.
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